Synthesis and antimuscarinic activity of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]aminoethyl 2,2-diphenylpropionate, a metabolite of aprophen.

doi:10.1002/JPS.2600820603

Paper

Synthesis and antimuscarinic activity of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]aminoethyl 2,2-diphenylpropionate, a metabolite of aprophen.

Published Jun 1, 1993 · N. Brown, H. Leader, L. Phillips

Journal of pharmaceutical sciences

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Abstract

The preparation of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]amino-ethyl 2,2-diphenylpropionate (1), a metabolite of aprophen [2-diethylaminoethyl 2,2-diphenylpropionate], is described. Hydrolysis of [2-(2-chloroethyl)ethylamino]ethyl acetate hydrochloride (2) in a basic solution, followed by acidic pH adjustment, gave the ethylcholineaziridinium ion (3) that upon treatment with 2,2-diphenylpropionic acid produced 1 in a 56% yield. Synthetic 1 was found to possess antimuscarinic activities, but was approximately 10-fold less potent than the parent compound aprophen.

Study Snapshot

2-[N-(ethyl)-(N-beta-hydroxyethyl)]amino-ethyl 2,2-diphenylpropionate (1), a metabolite of aprophen, possesses antimuscarinic activities but is approximately 10-fold less

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and antimuscarinic activity of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]aminoethyl 2,2-diphenylpropionate, a metabolite of aprophen.

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References

Binary antidotes for organophosphate poisoning: aprophen analogues that are both antimuscarinics and carbamates.

Carbaphen compounds show potential as effective organophosphate poisoning prophylaxis by inactivating butyrylcholinesterase and exhibiting antimuscarinic properties.

Desethylaprophen: a metabolite of aprophen with antimuscarinic activities.

Desethylaprophen, a major metabolite of aprophen, has antimuscarinic activities and can compete for binding sites of muscarinic receptors in guinea pig ileum, despite its lower biological effects.

A microtechnique for quantification of detergent‐solubilized muscarinic and nicotinic acetylcholine receptors using a semi‐automated cell harvester

This study presents a rapid method for assaying muscarinic and nicotinic acetylcholine receptors using a semi-automated cell harvester, enabling rapid screening of cholinergic agonists/antagonists and further purification and characterization of m

Disposition of aprophen in rats

Unchanged aprophen is largely responsible for its in-vivo actions, with rapid distribution to highly perfused organs and high plasma clearance due to a large volume of distribution and high metabolic rate.

Neuropathology and amphetamine-induced turning resulting from AF64A injections into the striatum of the rat.

AF64A injections into the striatum of rats cause disruption of normal pathways and can cause necrosis, highlighting the need to consider tissue damage when interpreting behavioral data.

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